Water → HCID 58565339, compound

HRID 2175349Notes

Reaction equation

HRID 2175349 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:4]=1[C:19]([O:21]C)=[O:20])#[N:2].[OH-].[Li+].O>CO.Cl>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:4]=1[C:19]([OH:21])=[O:20])#[N:2]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 58565377HCID 58565377, compound

Product 1

HCID 58565339HCID 58565339, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Methyl 3-cyano-1-(3-fluorophenyl)-1H-indole-2-carboxylate (0.13 g, 0.44 mmol) was treated with 1.0 M lithium hydroxide in water (0.66 mL, 0.66 mmol) in methanol (3 mL) at room temperature for 3 hours. The reaction was diluted with 1 N HCl and extracted with EtOAc. The extracts were combined, washed with brine, dried over MgSO4 and concentrated to give the desired acid (0.12 g, 97%). LCMS calculated for C16H10FN2O2(M+H)+: m/z=281.1. Found: 281.1.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-32a50abb8904480e9488e1aa801bee28
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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